アミノレブリン酸メチル

Methyl Aminolevulinate

HCID 157922

基本情報

CAS
33320-16-0
標準SMILES
COC(=O)CCC(=O)CN
InChIKey
YUUAYBAIHCDHHD-UHFFFAOYSA-N
分子式
C6H11NO3
平均分子量
145.16 g/mol
単同位体質量
145.07389321

概要

Methyl 5-aminolevulinate is the methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydrochloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells. It has a role as an antineoplastic agent, a photosensitizing agent, a dermatologic drug and a prodrug. It is functionally related to a 5-aminolevulinic acid.

名称と識別子

優先名称
Methyl Aminolevulinate
IUPAC
methyl 5-amino-4-oxopentanoate
現地名
アミノレブリン酸メチル
英語名
D-Aminolevulinicacidmethylesterhydrochloride
分子式
C6H12ClNO3
分子量
181.61738

名称と別名

Methyl aminolevulinatemethyl 5-amino-4-oxopentanoate33320-16-0methyl 5-aminolevulinate5-Aminolevulinic acid methyl estermethyl aminolaevulinatemethyl delta-aminolevulinateMAOP cpdMethylaminolevulinatePentanoic acid, 5-amino-4-oxo-, methyl ester585NM85KYMMethyl-5-aminolevulinate
名称をさらに表示
アミノレブリン酸メチルD-AminolevulinicacidmethylesterHCl
DTXSID3048570CHEBI:724125RefChem:157787DTXCID4028202MetvixAminolevulinic acid methyl esterNCGC00018251-03UNII-585NM85KYM

データベース識別子

CAS
33320-16-0
PubChem CID
157922
DTXSID
DTXSID3048570
ChEMBL
CHEMBL1096562
ChEBI
CHEBI:724125
UNII
585NM85KYM
Nikkaji
J313.797J

物性

構造計算による物性

XLogP
-1
極性表面積
69.4 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
5
重原子数
10

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.2
Solubility · 2 件

Freely soluble

2.20e+02 g/L

Physical DescriptionSolid

物理化学的性質

LogP
-0.57 · -0.570 (est)

化学と産業

薬理情報

ATC Code · 3 件

L01XD03

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1 件

After topical application of methyl aminolevulinate, porphyrins will accumulate intracellularly in the treated skin lesions. The intracellular porphyrins (including PpIX) are photoactive, fluorescing compounds and, upon light activation in the presence of oxygen, singlet oxygen is formed which causes damage to cellular compartments, in particular the mitochondria. Light activation of accumulated porphyrins leads to a photochemical reaction and thereby phototoxicity to the light-exposed target cells.

Mechanism of Action · 1 件

Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals.

FDA Pharmacological Classification · 5 件

585NM85KYM

METHYL AMINOLEVULINATE

Established Pharmacologic Class [EPC] - Porphyrin Precursor

Chemical Structure [CS] - Porphyrinogens

Methyl aminolevulinate is a Porphyrin Precursor.

MeSH Pharmacological Classification · 1 件

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.

Absorption, Distribution and ExcretionIn vitro, after 24 hours the mean cumulative absorption through human skin was 0.26% of the administered dose.

サプライヤー11 社

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
補足説明 · 1 件

定義ChEBI: The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydro hloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills t e tumour cells.

関連反応

5 件

化合物ノート

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